Cross-Strait relations are at a crossroads, and there may be a peaceful way out: a hybrid of federation and confederation. However, such an association, or any other kind of integration, is faced with obstacles such as the difficulty for people to cross (sub) cultural boundaries in order to overcome their prejudices and discriminatory attitudes, and the difficulty of reconciling political realism on the one hand and cosmopolitanism and idealism on the other. This paper examines these obstacles. While discussing them, it analyzes the political, economic, and cultural forces that together affect the direction of future cross-Strait relations. The paper points out that ultimately the future depends on both sides' efforts and ability to negotiate their differences and find a balance between individuality and humanity. It is not going to be easy. In its examination of these issues, the paper uses the historical-comparative method, supported by textual analysis of policy statements of the parties involved.